Hydrochloric Acid → (3-Fluoro-5-nitrophenyl)methanol

HRID 1690489Notes

Reaction equation

HRID 1690489 reaction equation
[BH4-].[Li+].C[O:4][C:5](=O)[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([F:15])[CH:7]=1.C(OCC)C.Cl>O>[F:15][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=1)[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 43449025Methyl 3-fluoro-5-nitrobenzoate

Product 1

HCID 66907232(3-Fluoro-5-nitrophenyl)methanolYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of lithium borohydride (2M in THF, 7.3 ml) was added slowly to a mixture of methyl-3-fluoro-5-nitrobenzoate (JCS Chem. Comm., 1993, 921-922; 2.9 g) and diethyl ether (60 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. Water and a 2N aqueous hydrochloric acid solution were added in turn and the mixture was extracted with diethyl ether. The organic solution was evaporated and the residue was purified by column chromatography on silica using methylene chloride as eluent. There was thus obtained an oil which crystallised on standing to give 3-fluoro-5-nitrobenzyl alcohol (2.05 g); 1H NMR: (DMSOd6) 4.64 (s, 2H), 5.65 (s, 1H), 7.64 (m, 1H), 7.96 (m, 1H), 8.06 (s, 1H).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. customThe organic solution was evaporated
  3. customthe residue was purified by column chromatography on silica
  4. customThere was thus obtained an oil which
  5. customcrystallised

Sources & evidence

ORD record
ord-727bd5e87ad74dafb882b4c67a399ded
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

Loading…